JPH0459878A - Powder coating composition - Google Patents
Powder coating compositionInfo
- Publication number
- JPH0459878A JPH0459878A JP2171897A JP17189790A JPH0459878A JP H0459878 A JPH0459878 A JP H0459878A JP 2171897 A JP2171897 A JP 2171897A JP 17189790 A JP17189790 A JP 17189790A JP H0459878 A JPH0459878 A JP H0459878A
- Authority
- JP
- Japan
- Prior art keywords
- resin
- acid
- weight
- parts
- composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000843 powder Substances 0.000 title claims abstract description 50
- 239000008199 coating composition Substances 0.000 title claims description 10
- 229920005989 resin Polymers 0.000 claims abstract description 52
- 239000011347 resin Substances 0.000 claims abstract description 52
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 27
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 15
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 14
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 13
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 13
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims abstract description 13
- 239000011342 resin composition Substances 0.000 claims abstract description 13
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000004593 Epoxy Substances 0.000 claims abstract description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003822 epoxy resin Substances 0.000 claims abstract description 12
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 11
- 239000004645 polyester resin Substances 0.000 claims abstract description 10
- 229920001225 polyester resin Polymers 0.000 claims abstract description 10
- 230000009477 glass transition Effects 0.000 claims abstract description 9
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 8
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims abstract description 8
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims abstract description 7
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims abstract description 7
- 239000011976 maleic acid Substances 0.000 claims abstract description 7
- 239000001530 fumaric acid Substances 0.000 claims abstract description 6
- 125000000466 oxiranyl group Chemical group 0.000 claims abstract description 6
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000002378 acidificating effect Effects 0.000 claims abstract description 5
- 239000003973 paint Substances 0.000 claims description 22
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 19
- 239000000178 monomer Substances 0.000 claims description 19
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 11
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000007334 copolymerization reaction Methods 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 52
- 239000011248 coating agent Substances 0.000 abstract description 35
- 150000001875 compounds Chemical class 0.000 abstract description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 238000013329 compounding Methods 0.000 abstract 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 20
- 230000000704 physical effect Effects 0.000 description 14
- 239000002253 acid Substances 0.000 description 12
- -1 polyethylene Polymers 0.000 description 11
- 229910052742 iron Inorganic materials 0.000 description 10
- 239000011574 phosphorus Substances 0.000 description 9
- 229910052698 phosphorus Inorganic materials 0.000 description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 7
- 239000000654 additive Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- LKMJVFRMDSNFRT-UHFFFAOYSA-N 2-(methoxymethyl)oxirane Chemical compound COCC1CO1 LKMJVFRMDSNFRT-UHFFFAOYSA-N 0.000 description 2
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 229920006243 acrylic copolymer Polymers 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- FJTUUPVRIANHEX-UHFFFAOYSA-N butan-1-ol;phosphoric acid Chemical compound CCCCO.OP(O)(O)=O FJTUUPVRIANHEX-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- UFDHBDMSHIXOKF-UHFFFAOYSA-N cyclohexene-1,2-dicarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- LAYAKLSFVAPMEL-UHFFFAOYSA-N 1-ethenoxydodecane Chemical compound CCCCCCCCCCCCOC=C LAYAKLSFVAPMEL-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical group CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- BQBSIHIZDSHADD-UHFFFAOYSA-N 2-ethenyl-4,5-dihydro-1,3-oxazole Chemical compound C=CC1=NCCO1 BQBSIHIZDSHADD-UHFFFAOYSA-N 0.000 description 1
- LJKDOMVGKKPJBH-UHFFFAOYSA-N 2-ethylhexyl dihydrogen phosphate Chemical compound CCCCC(CC)COP(O)(O)=O LJKDOMVGKKPJBH-UHFFFAOYSA-N 0.000 description 1
- CLDHCTYNLBCYCW-UHFFFAOYSA-N 2-ethyloctyl 2-methylprop-2-enoate Chemical compound CCCCCCC(CC)COC(=O)C(C)=C CLDHCTYNLBCYCW-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 description 1
- OZFLRNPZLCUVFP-UHFFFAOYSA-N 8-methylnonyl dihydrogen phosphate Chemical compound CC(C)CCCCCCCOP(O)(O)=O OZFLRNPZLCUVFP-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920012485 Plasticized Polyvinyl chloride Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- GHPGOEFPKIHBNM-UHFFFAOYSA-N antimony(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Sb+3].[Sb+3] GHPGOEFPKIHBNM-UHFFFAOYSA-N 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- BNMJSBUIDQYHIN-UHFFFAOYSA-N butyl dihydrogen phosphate Chemical compound CCCCOP(O)(O)=O BNMJSBUIDQYHIN-UHFFFAOYSA-N 0.000 description 1
- CJOBVZJTOIVNNF-UHFFFAOYSA-N cadmium sulfide Chemical compound [Cd]=S CJOBVZJTOIVNNF-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 229940072282 cardura Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- JBSLOWBPDRZSMB-BQYQJAHWSA-N dibutyl (e)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C\C(=O)OCCCC JBSLOWBPDRZSMB-BQYQJAHWSA-N 0.000 description 1
- OGVXYCDTRMDYOG-UHFFFAOYSA-N dibutyl 2-methylidenebutanedioate Chemical compound CCCCOC(=O)CC(=C)C(=O)OCCCC OGVXYCDTRMDYOG-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZEFVHSWKYCYFFL-UHFFFAOYSA-N diethyl 2-methylidenebutanedioate Chemical compound CCOC(=O)CC(=C)C(=O)OCC ZEFVHSWKYCYFFL-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- TVACALAUIQMRDF-UHFFFAOYSA-N dodecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCOP(O)(O)=O TVACALAUIQMRDF-UHFFFAOYSA-N 0.000 description 1
- RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 1
- 238000009503 electrostatic coating Methods 0.000 description 1
- 238000007590 electrostatic spraying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229920006334 epoxy coating Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BNKAXGCRDYRABM-UHFFFAOYSA-N ethenyl dihydrogen phosphate Chemical compound OP(O)(=O)OC=C BNKAXGCRDYRABM-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- UCNNJGDEJXIUCC-UHFFFAOYSA-L hydroxy(oxo)iron;iron Chemical compound [Fe].O[Fe]=O.O[Fe]=O UCNNJGDEJXIUCC-UHFFFAOYSA-L 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- PIJPYDMVFNTHIP-UHFFFAOYSA-L lead sulfate Chemical compound [PbH4+2].[O-]S([O-])(=O)=O PIJPYDMVFNTHIP-UHFFFAOYSA-L 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- PSCWDXZBRYGBDI-UHFFFAOYSA-N n-(oxiran-2-ylmethyl)prop-2-enamide Chemical compound C=CC(=O)NCC1CO1 PSCWDXZBRYGBDI-UHFFFAOYSA-N 0.000 description 1
- AWIZFKXFPHTRHN-UHFFFAOYSA-N naphtho[2,3-f]quinoline Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=N1 AWIZFKXFPHTRHN-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- YOURXVGYNVXQKT-UHFFFAOYSA-N oxacycloundecane-2,11-dione Chemical compound O=C1CCCCCCCCC(=O)O1 YOURXVGYNVXQKT-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- YCNNCJXFNCVEOL-UHFFFAOYSA-N oxiran-2-ylmethyl ethenesulfonate Chemical compound C=CS(=O)(=O)OCC1CO1 YCNNCJXFNCVEOL-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 238000007751 thermal spraying Methods 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/062—Copolymers with monomers not covered by C09D133/06
- C09D133/068—Copolymers with monomers not covered by C09D133/06 containing glycidyl groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/062—Copolymers with monomers not covered by C08L33/06
- C08L33/064—Copolymers with monomers not covered by C08L33/06 containing anhydride, COOH or COOM groups, with M being metal or onium-cation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/934—Powdered coating composition
Abstract
Description
【発明の詳細な説明】
技術分野
本発明は粉体塗料組成物に係り、さらに詳しくは平滑性
、・光沢性、鮮映性等に優れた硬化塗膜を与えうる粉体
塗料組成物に関するものである。DETAILED DESCRIPTION OF THE INVENTION Technical Field The present invention relates to a powder coating composition, and more particularly to a powder coating composition capable of providing a cured coating film with excellent smoothness, gloss, sharpness, etc. It is.
従来技術
粉体塗料は一般に流動浸漬法、静電塗装法、粉体散布、
溶射法、フロックガン等各種方法で被塗物に適用されそ
れぞれの塗装法に適した各種樹脂組成物、例えば可塑化
ＰＶＣ、ポリエチレン、ナイロン、ポリエステル、セル
ロース系、エポキシ樹脂、塩素化ポリエーテル、ポリウ
レタン、フッ素樹脂等をビヒクルとする粉体塗料が広く
用いられている。中でもビニル系樹脂は耐薬品性、耐摩
耗性、高電気的特性がよく安価なので広く実用化され、
またエポキシ樹脂はジシアンジアミド、芳香族アミン、
アミンコンプレックス、酸無水物、フェノール樹脂／酸
触媒等の硬化剤と共に用い耐薬品性、強じん性、付着性
、耐候性、耐熱性、耐摩耗性、電気的特性に優れた塗膜
を与えうるため広範囲に使用されている。Conventional powder coatings generally use fluidized dipping, electrostatic coating, powder spraying,
Various resin compositions suitable for each coating method, such as plasticized PVC, polyethylene, nylon, polyester, cellulose, epoxy resin, chlorinated polyether, polyurethane, which are applied to objects to be coated by various methods such as thermal spraying and flocking. Powder coatings using a vehicle such as fluororesin or the like are widely used. Among them, vinyl resin has good chemical resistance, abrasion resistance, high electrical properties, and is inexpensive, so it has been widely put into practical use.
In addition, epoxy resins include dicyandiamide, aromatic amines,
Can be used with curing agents such as amine complexes, acid anhydrides, phenolic resins/acid catalysts, etc. to provide coatings with excellent chemical resistance, toughness, adhesion, weather resistance, heat resistance, abrasion resistance, and electrical properties. Because of this, it is widely used.
こういった粉体塗料は溶剤型の塗料に比し衛生公害面で
優れその用途が益々広がりつつあるが、−般に塗面平滑
性、光沢、鮮映性等に問題があり、特に自動車上塗り塗
料としては不充分でそれら特性の改善が強く望まれてい
る。These powder coatings are superior to solvent-based paints in terms of hygiene and pollution, and their uses are becoming more and more widespread. It is insufficient as a paint, and there is a strong desire to improve these properties.
平滑性、光沢、鮮映性、耐候性等の改善された硬化塗膜
を与える粉体塗料組成物を得るため各種研究がなされ、
例えば特開昭５６−８６４号および特開昭５９−１２０
６６６号記載の如きグリシジル基含有ビニルモノマー、
リン酸エステルビニルモノマーを構成成分として含む特
定の軟化点および数平均分子量をもつビニル系共重合体
と、脂肪族二塩基酸とからなる熱硬化型の粉体塗料組成
物、特開昭５６−４７４５６号記載の如き架橋性官能基
を有し７０〜１５０℃の軟化点、２０００〜３００００
の数平均分子量を有する含リンビニル系重合体と硬化剤
を主成分とする粉体塗料用樹脂組成物、特開昭５７−８
７４７１号記載の如き、含リン高分子添加剤を０．０１
〜１０重量％含む熱硬化性樹脂からなる塗体塗料組成物
などが特に注目されてきた。Various studies have been conducted to obtain powder coating compositions that provide cured coatings with improved smoothness, gloss, sharpness, weather resistance, etc.
For example, JP-A-56-864 and JP-A-59-120
Glycidyl group-containing vinyl monomers as described in No. 666,
Thermosetting powder coating composition comprising a vinyl copolymer having a specific softening point and number average molecular weight containing a vinyl phosphate monomer as a constituent component, and an aliphatic dibasic acid, JP-A-56- It has a crosslinkable functional group as described in No. 47456, has a softening point of 70 to 150°C, and has a softening point of 2,000 to 30,000.
A resin composition for powder coatings containing as main components a phosphorus-containing vinyl polymer having a number average molecular weight of
0.01 of the phosphorus-containing polymer additive as described in No. 7471.
Particular attention has been paid to coating compositions comprising thermosetting resins containing up to 10% by weight of thermosetting resins.
しかしながらこれらはいづれもリン含有バインダー樹脂
、あるいはリン含有高分子添加剤を利用する技術で要求
品質によっては尚効果が不充分であり、また公衆衛生、
公害、環境保全の見地からはリンによらぬ、あるいはリ
ン使用量の少ない粉体塗料であることが好ましく、自動
車上塗りとしてさらに一段と優れた平滑性、光沢、鮮映
性、耐候性を有する硬化塗膜を与えうるものが要求され
ている。However, all of these technologies use phosphorus-containing binder resins or phosphorus-containing polymer additives, and depending on the required quality, they are still insufficiently effective, and they are also harmful to public health.
From the standpoint of pollution and environmental conservation, it is preferable to use powder coatings that do not contain phosphorus or use a small amount of phosphorus, and cured coatings that have even better smoothness, gloss, sharpness, and weather resistance as automotive topcoats. There is a need for something that can provide a film.
発明が解決しようとする問題点
そこでリン酸エステル含有ポリマーあるいは高リン含有
重合体添加剤にたよることなく特に自動車上塗りとして
好適な平滑性、光沢、鮮映性、耐候性に優れた硬化塗膜
を与えうる粉体塗料を提供することが本発明目的である
。The problem to be solved by the invention is to provide a cured coating film with excellent smoothness, gloss, sharpness, and weather resistance that is particularly suitable as an automotive topcoat without relying on phosphate ester-containing polymers or high phosphorus-containing polymer additives. It is an object of the present invention to provide a powder coating that can provide the following properties.
問題点を解決するための手段
本発明に従えば上記目的が１分子中に２以上のオキシラ
ン基を有する基体樹脂と、エポキシ用の硬化剤とからな
る熱硬化性塗体塗料用樹脂組成物にチオリンゴ酸、マレ
イン酸、フマル酸およびイタコン酸からなる群より選ば
れる少なくとも１種の脂肪族ジカルボン酸成分を重量比
で１〜１０％含む数平均分子量１０００〜８０００、ガ
ラス転移温度−４０〜１００℃のビニル樹脂を０．５〜
１０重量％配合してなる樹脂組成物を樹脂成分として含
む粉体塗料組成物により達成せられる。
゛本発明においては、熱硬化型の粉体塗料樹脂組成
物として、分子中に２以上のオキシラン基を有する基体
樹脂と、エポキシ用硬化剤の組合わせが用いられる０分
子中に２以上のオキシラン基を有する粉体塗料用の樹脂
としては、例えばグリシジル基を有するアクリル樹脂、
エポキシ樹脂、グリシジル基を有するポリエステル樹脂
等が好適に使用せられるが、より詳しくは下記の如き基
体樹脂が有用である。Means for Solving the Problems According to the present invention, the above object is achieved by providing a resin composition for thermosetting paints comprising a base resin having two or more oxirane groups in one molecule and a curing agent for epoxy. Contains 1 to 10% by weight of at least one aliphatic dicarboxylic acid component selected from the group consisting of thiomalic acid, maleic acid, fumaric acid and itaconic acid, number average molecular weight 1000 to 8000, glass transition temperature -40 to 100°C of vinyl resin from 0.5 to
This can be achieved by using a powder coating composition containing 10% by weight of a resin composition as a resin component.
゛In the present invention, as a thermosetting powder coating resin composition, a combination of a base resin having two or more oxirane groups in the molecule and a curing agent for epoxy is used. Examples of resins for powder coatings having groups include acrylic resins having glycidyl groups,
Epoxy resins, polyester resins having glycidyl groups, and the like are preferably used, and more specifically, the following base resins are useful.
（１）アクリル樹脂
グリシジル基含有単量体を２０〜５０重量％とその他の
エチレン系不飽和単量体８０〜５０重量％を共重合して
なり、かつ３０〜７５℃の範囲のガラス転移温度と、１
５００〜１００００の範囲の数平均分子量を有するアク
リル系共重合体。(1) Acrylic resin obtained by copolymerizing 20 to 50% by weight of a glycidyl group-containing monomer and 80 to 50% by weight of other ethylenically unsaturated monomers, and having a glass transition temperature in the range of 30 to 75°C. and 1
An acrylic copolymer having a number average molecular weight in the range of 500 to 10,000.
上記のアクリル系共重合体中にグリシジル基を与えるも
のとして使用されるグリシジル基含有単量体としては（
メタ）アクリル酸の（メチル）グリシジルエステル、（
メタ）ア、リルアルコールの（メチル）グリシジルエー
テル、Ｎ−グリシジルアクリル酸アミド、ビニルスルフ
オン酸グリシジル等があり、これらは１種または２種以
上の混合物として使用できる。The glycidyl group-containing monomer used to provide the glycidyl group in the above acrylic copolymer is (
(Methyl)glycidyl ester of meth)acrylic acid, (
Examples include (methyl)glycidyl ether of meth)alcohol, N-glycidyl acrylic acid amide, glycidyl vinylsulfonate, and these can be used alone or in a mixture of two or more.
一方、グリシジル基含有単量体と共重合させる単量体と
してはグリシジル基と反応しないもの、例えば混合、混
線時の温度に於いては、グリシジル基と反応性の無いも
のであって、かつ上記のグリシジル基含有単量体とラジ
カル的に共重合する単量体、例えば、アクリル酸エステ
ル、メタクリル酸エステル、及びその他のエチレン系不
飽和単量、体があり、単独もしくは混合物として使用さ
れる。On the other hand, the monomer to be copolymerized with the glycidyl group-containing monomer is one that does not react with the glycidyl group, for example, one that has no reactivity with the glycidyl group at the temperature during mixing and crosstalk, and There are monomers that radically copolymerize with the glycidyl group-containing monomers, such as acrylic esters, methacrylic esters, and other ethylenically unsaturated monomers, which can be used alone or in mixtures.
アクリル酸またはメタクリル酸のエステルとしては、例
えばアクリル酸メチル、アクリル酸エチル、アクリル酸
ｎ−プロピル、アクリル酸イソプロピル、アクリル酸ｎ
−ブチル、アクリル酸イソブチル、アクリル酸ｔｅｒｔ
−ブチル、アクリル酸シクロヘキシル、アクリル酸２−
エチルヘキシル、アクリル酸オクチル、アクリル酸２−
エチルオクチル、アクリル酸ドデシル、アクリル酸ベン
ジル、メタクリル酸メチル、メタクリル酸エチル、メタ
クリル酸ｎ−プロピル、メタクリル酸イソプロピル、メ
タクリル酸ｎ−ブチル、メタクリル酸イソブチル、メタ
クリル酸ｔｅｒｔ−ブチル、・メタクリル酸ヘキシル、
メタクリル酸シクロヘキシル、メタクリル酸２−エチル
ヘキシル、メタクリル酸オクチル、メタクリル酸２−エ
チルオクチル、メタクリル酸ベンジル、メタクリル酸ド
デシル、メタクリル酸フェニル、アクリル酸２−ヒドロ
キシエチル、メタクリル酸２−ヒドロキシエチル、アク
リル酸２−ヒドロキシプロピル、メタクリル酸２−ヒド
ロキシプロピル等があげられる。Examples of esters of acrylic acid or methacrylic acid include methyl acrylate, ethyl acrylate, n-propyl acrylate, isopropyl acrylate, and n-acrylate.
-butyl, isobutyl acrylate, tert acrylate
-butyl, cyclohexyl acrylate, acrylic acid 2-
Ethylhexyl, octyl acrylate, acrylic acid 2-
Ethyl octyl, dodecyl acrylate, benzyl acrylate, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, tert-butyl methacrylate, hexyl methacrylate,
Cyclohexyl methacrylate, 2-ethylhexyl methacrylate, octyl methacrylate, 2-ethyloctyl methacrylate, benzyl methacrylate, dodecyl methacrylate, phenyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-acrylic acid -hydroxypropyl, 2-hydroxypropyl methacrylate, etc.
又、その他のエチレン系不飽和単量体としては、フマル
酸ジエチル、フマル酸ジブチル等のフマル酸ジアルキル
エステル、イタコン酸ジエチル、イタコン酸ジブチル等
のイタコン酸ジアルキルエステル、スチレン、ビニルト
ルエン、α−メチルスチレン、アクリロニトリル、メタ
クリロニトリル、アクリルアミド、メタクリルアミド、
メチロールアクリルアミド、アルコキシメチロールアミ
ド、ビニルオキサゾリン、酢酸ビニル、プロピオン酸ビ
ニル、ラウリルビニルエーテル等があげられる。Other ethylenically unsaturated monomers include dialkyl fumarate esters such as diethyl fumarate and dibutyl fumarate, dialkyl itaconate esters such as diethyl itaconate and dibutyl itaconate, styrene, vinyltoluene, and α-methyl. Styrene, acrylonitrile, methacrylonitrile, acrylamide, methacrylamide,
Examples include methylol acrylamide, alkoxymethylolamide, vinyloxazoline, vinyl acetate, vinyl propionate, and lauryl vinyl ether.
上記アクリル酸エステル、メタクリル酸エステル及びそ
の他のエチレン系不飽和単量体は１種または２種以上の
混合物として使用できる。The above acrylic esters, methacrylic esters, and other ethylenically unsaturated monomers can be used alone or as a mixture of two or more.
（２ポリエステル樹脂
塗料関係で一般に用いられるポリエステル樹脂を変性し
てエポキシ基を一部に付加させたもの、もしくはポリエ
ステル合成時にエポキシ基を導入したものを本発明に適
用する。(2) Polyester resins Polyester resins commonly used in paints are modified to have epoxy groups added to some of them, or epoxy groups are introduced during polyester synthesis, which are applied to the present invention.
当該ポリエステル樹脂を得るにさいして用いられる多価
アルコールの代表例としては、エチレングリコール、プ
ロピレングリコール、ネオペンチルグリコール、１．６
−ヘキサンジオール、１．３−ブチレングリコール、１
．４−ブチレングリコール、ビス（ヒドロキシエチル）
テレフタレート、水添ビスフェノールＡ、トリメチロー
ルエタン、トリメチロールプロパン、グリセリン、ペン
タエリスリトール、１．４−シクロヘキサンジメタツー
ルまたはそれらのアルキレンオキサイド付加物さらには
「カーデュラＥ」などのエポキシ化合物が挙げられ、他
方、−価カルボン酸および多価カルボン酸の代表例とし
てはフタル酸、イソフタル酸、テレフタル酸、ヘット酸
、トリメリット酸、コハク酸、シュウ酸、アジピン酸、
セバシン酸、安息香酸、Ｐ ｔｅｒｔ−ブチル安息香
酸、ｐ−ヒドロキシ安息香酸または（メタ）アクリル酸
などが、さらにはそれらの無水物、水添物もしくはメチ
ルエステル物が挙げられる。 ゛ □
・・これらにエポキシ基を導入する方法は、いかなる手
法を用いてもよいが、たとえば多官能エポキシを付加す
ることによって、一部にエポキシ基を導入する方法は、
簡便な方法の１つであろう。Typical examples of polyhydric alcohols used to obtain the polyester resin include ethylene glycol, propylene glycol, neopentyl glycol, 1.6
-hexanediol, 1,3-butylene glycol, 1
．． 4-Butylene glycol, bis(hydroxyethyl)
Examples include terephthalate, hydrogenated bisphenol A, trimethylolethane, trimethylolpropane, glycerin, pentaerythritol, 1,4-cyclohexane dimetatool or their alkylene oxide adducts, as well as epoxy compounds such as "Cardura E"; Typical examples of -valent carboxylic acids and polyvalent carboxylic acids include phthalic acid, isophthalic acid, terephthalic acid, het's acid, trimellitic acid, succinic acid, oxalic acid, adipic acid,
Examples include sebacic acid, benzoic acid, P tert-butylbenzoic acid, p-hydroxybenzoic acid, and (meth)acrylic acid, as well as anhydrides, hydrogenated products, and methyl esters thereof.゛ □
...Any method may be used to introduce epoxy groups into these, but for example, a method of introducing epoxy groups into a part by adding a polyfunctional epoxy is as follows:
This would be one of the simplest methods.
（３）エポキシ樹脂
アルキル基の炭素数１〜８のアルキルグリシジルエーテ
ル、アリルグリシジルエーテル、フェニルグリシジルエ
ーテル、スチレンオキサイド、アルキル基の炭素数１〜
４のアルキルフェニルグリシジルエーテル、パーサティ
ック酸グリシジルエステル等のモノエポキシド、アルキ
レン基の炭素数４〜６のアルキレングリシジルエーテル
型エポキシ樹脂、ビスフェノールグリシジルエーテル型
エポキシ樹脂、ビスフェノールメチルグリシジルエーテ
ル型エポキシ樹脂、ノボラック型エポキシ樹脂等のジー
又はポリエポキシド及びこれらのジー又はポリエポキシ
ド中のエポキシ基の一部を油脂肪酸、安息香酸、アクリ
ル酸またはメタクリル酸でエステル化して得られるエポ
キシエステル化物等から選ばれた１種あるいは、２種以
上を用いたもの。(3) Epoxy resin alkyl group having 1 to 8 carbon atoms, alkyl glycidyl ether, allyl glycidyl ether, phenyl glycidyl ether, styrene oxide, alkyl group having 1 to 8 carbon atoms
Monoepoxides such as alkylphenyl glycidyl ether of 4, persatic acid glycidyl ester, alkylene glycidyl ether type epoxy resin with an alkylene group having 4 to 6 carbon atoms, bisphenol glycidyl ether type epoxy resin, bisphenol methyl glycidyl ether type epoxy resin, novolak type One type selected from di- or polyepoxides such as epoxy resins and epoxy esterified products obtained by esterifying a part of the epoxy groups in these di- or polyepoxides with oil fatty acids, benzoic acid, acrylic acid or methacrylic acid, or Those using two or more types.
等がいづれも好適に使用せられる。etc. can be suitably used.
尚本発明に於いては、必ずしも必須ではないが、分子中
に２以上のオキシラン基を有する基体樹脂を１０５〜１
０重量％、好ましくは０．１〜５％までの酸性リン酸エ
ステルでリン変性したものを用いることもできる。リン
変性に使用せられる酸性リン酸エステルとしては例えば
メチルアシドホスフェート、イソプロピルアシドホスフ
ェート、ブチルアシドホスフェート、ジブチルホスフェ
ート、モノブチルホスフェート、２−エチルへキシルア
シドホスフェート、ジー２−エチルへキシルホスフェー
ト、イソデシルアシドホスフェート、モノイソデシルホ
スフェート、ドデシルアシドホスフェート等が好適に用
いられる。この場合、粉体塗料の分散性、耐水性等を考
慮し、酸性リン酸エステル変性を行う場合、その量は基
体樹脂に対し０．０５〜１０％内、好ましくは０．１〜
５％の範囲内とすることが好ましい。In the present invention, although not necessarily essential, the base resin having two or more oxirane groups in the molecule is used in the range of 105 to 1
It is also possible to use phosphorus modified with 0% by weight, preferably 0.1 to 5% of acidic phosphoric acid ester. Examples of acidic phosphate esters used for phosphorus modification include methyl acid phosphate, isopropyl acid phosphate, butyl acid phosphate, dibutyl phosphate, monobutyl phosphate, 2-ethylhexyl acid phosphate, di-2-ethylhexyl phosphate, and isodecyl. Acid phosphate, monoisodecyl phosphate, dodecyl acid phosphate, etc. are preferably used. In this case, in consideration of the dispersibility, water resistance, etc. of the powder coating, when modifying the acidic phosphate ester, the amount should be within 0.05 to 10%, preferably 0.1 to 10%, based on the base resin.
It is preferably within the range of 5%.
エポキシ用硬化剤としてはアミン系化合物も常温固体で
反応性のあまり大でないものであれば使用可能であるが
、粉体塗料用としては酸無水物、多塩基酸等が最も好適
であり、例えばグルタル酸、アジピン酸、ピメリン酸、
スペリン酸、アゼライン酸、セバシン酸、１．１２−ド
デカン２酸、１．２０−アイコサン２酸、クエン酸、マ
レイン酸、シトラコン酸、イタコン酸、グルタコン酸、
フタル酸、イソフタル酸、ヘキサヒドロフタル酸、シク
ロヘキセン１，２−ジカルボン酸などの多価カルボン酸
があげられる。また無水コハク酸、無水セバシン酸、無
水フタル酸、無水イタコン酸、無水トリメリット酸など
の如き、多価カルボン酸無水物であってもよく、また１
分子中に２個以上のカルボキシル基を有するポリエステ
ルであってもかまわない。As a curing agent for epoxy, amine compounds can be used as long as they are solid at room temperature and are not very reactive, but for powder coatings, acid anhydrides, polybasic acids, etc. are most suitable. glutaric acid, adipic acid, pimelic acid,
Speric acid, azelaic acid, sebacic acid, 1.12-dodecanedioic acid, 1.20-icosanedioic acid, citric acid, maleic acid, citraconic acid, itaconic acid, glutaconic acid,
Examples include polycarboxylic acids such as phthalic acid, isophthalic acid, hexahydrophthalic acid, and cyclohexene 1,2-dicarboxylic acid. It may also be a polyhydric carboxylic acid anhydride such as succinic anhydride, sebacic anhydride, phthalic anhydride, itaconic anhydride, trimellitic anhydride, etc.
It may be a polyester having two or more carboxyl groups in the molecule.
本発明にあっては上記の基体樹脂と硬化剤とからなる熱
硬化型の粉体塗料用樹脂組成物に対し、特定量の特定ビ
ニル樹脂が平滑性、光沢、鮮映性改善目的で添加せられ
ることを特徴とするものである。In the present invention, a specific amount of a specific vinyl resin is added to the thermosetting resin composition for powder coating consisting of the above-mentioned base resin and curing agent for the purpose of improving smoothness, gloss, and image clarity. It is characterized by being
本発明で上記目的で添加せられるビニル樹脂は、チオリ
ンゴ酸、マレイン酸、フマル酸、イタコン酸からなる群
より選ばれる介在炭素数１〜２の脂肪族ジカルボン酸を
その構成成分として１〜１０重量％含むビニル樹脂で、
数平均分子量が１０θθ〜８０００で、ガラス転移温度
が一４０〜１００℃の範囲内にある化合物である。The vinyl resin added for the above purpose in the present invention contains 1 to 10% by weight of an aliphatic dicarboxylic acid having 1 to 2 intervening carbon atoms selected from the group consisting of thiomalic acid, maleic acid, fumaric acid, and itaconic acid. Vinyl resin containing %,
It is a compound having a number average molecular weight of 10θθ to 8000 and a glass transition temperature within the range of 140 to 100°C.
かかるビニル樹脂はチオリンゴ酸の場合はビニル系モノ
マーの重合に際し、所定量のチオリンゴ酸を重合調節剤
に使用し、連鎖末端に鎖酸を存在せしめることができ、
また不飽和ジカルボン酸のマレイン酸、フマル酸、イタ
コン酸の場合はビニル系モノマーの一種として存在させ
、連鎖骨格中にこれらの酸を組みこむことができる。In the case of such a vinyl resin, a predetermined amount of thiomalic acid can be used as a polymerization regulator during polymerization of a vinyl monomer, and a chain acid can be present at the chain end.
In the case of unsaturated dicarboxylic acids such as maleic acid, fumaric acid, and itaconic acid, these acids can be present as a type of vinyl monomer and incorporated into the chain skeleton.
従って、かかるビニル樹脂はα、β−エチレン性不飽和
単量体で上記脂肪族不飽和ジカルボン酸以外のもの、あ
るいはそれらα、β−エチレン性不飽和単量体と脂肪族
不飽和ジカルボン酸とを通常の重合触媒、重合調整剤を
用い重合せしめる常法により容易に製造することができ
、そのガラス転移温度は使用する単量体の種類と割合に
より、また数平均分子量は重合条件、重合調節剤の選択
により自由に制御可能である。Therefore, such vinyl resins may contain α,β-ethylenically unsaturated monomers other than the above-mentioned aliphatic unsaturated dicarboxylic acids, or those α,β-ethylenically unsaturated monomers and aliphatic unsaturated dicarboxylic acids. can be easily produced by a conventional polymerization method using a conventional polymerization catalyst and polymerization modifier, and its glass transition temperature depends on the type and proportion of the monomers used, and the number average molecular weight depends on the polymerization conditions and polymerization control. It can be freely controlled by selecting the agent.
しかしながら本発明で添加剤として使用せられる上記ビ
ニル樹脂は、チオリンゴ酸、マレイン酸、フマル酸、イ
タコン酸から選ばれる介在炭素数１〜２の脂肪族ジカル
ボン酸が樹脂骨格中に１〜１０重量％の割合で含まれる
ことが必要である。このような酸の存在がいかなる理由
で硬化塗膜の平滑性、光沢、鮮映性の著しい改善に寄与
するものか正確な理由は未だ解明されていないが、本発
明者らは、これらの酸基が粉体塗料の硬化反応時に反応
しビニル樹脂自体が硬化塗膜樹脂に一体となり結合せら
れるだけでなく、ジカルボン酸酸基とビニル樹脂主鎖と
の極性、非極性に基づいてビニル樹脂自体が界面活性剤
の如く塗膜表面に局在し得るがため硬化塗膜の平滑性、
光沢、鮮映性の改善に寄与するものと考えている。However, the vinyl resin used as an additive in the present invention has 1 to 10% by weight of an intervening aliphatic dicarboxylic acid having 1 to 2 carbon atoms selected from thiomalic acid, maleic acid, fumaric acid, and itaconic acid in the resin skeleton. It is necessary to include the following proportions. Although the exact reason why the presence of such acids contributes to significant improvements in the smoothness, gloss, and sharpness of cured coatings has not yet been elucidated, the present inventors have found that the presence of these acids The groups react during the curing reaction of the powder coating, and the vinyl resin itself is not only integrated and bonded to the cured coating resin, but also the vinyl resin itself is can be localized on the coating surface like a surfactant, which reduces the smoothness of the cured coating.
We believe that this contributes to improving gloss and image clarity.
いづれにせよ、本発明者らは、上記特定の酸が特定量ビ
ニル樹脂中に存在することが必要で、この割合が１重量
％未満では塗膜外観の向上効果が認められす、１０重量
をこえると、外観向上の点では効果があるが、塗膜の耐
候性、耐衝撃性等の物性が低下し望ましくないことを見
出している。In any case, the present inventors have found that it is necessary for the above-mentioned specific acid to be present in a specific amount in the vinyl resin, and that when this proportion is less than 1% by weight, an effect of improving the appearance of the coating film is observed. It has been found that if it exceeds this, although it is effective in terms of improving the appearance, physical properties such as weather resistance and impact resistance of the coating film deteriorate, which is undesirable.
またビニル樹脂のガラス転移温度が一４０℃未満では耐
候性、耐衝撃性が低下し、１００℃をこえると外観向上
効果が低下すること、数平均分子量が１０００未満では
耐衝撃性等の物性が低下し、８０００をこえると外観向
上効果が低下するところから、ビニル樹脂のガラス転移
温度は一４０℃〜１００℃の範囲内、数平均分子量は１
０００〜８０００の範囲内、好ましくは２０００〜６０
００の範囲内であるべきことも見出された。Furthermore, if the glass transition temperature of vinyl resin is less than 140°C, weather resistance and impact resistance will decrease, if it exceeds 100°C, the appearance improvement effect will decrease, and if the number average molecular weight is less than 1000, physical properties such as impact resistance will deteriorate. If it exceeds 8000, the appearance improvement effect decreases, so the glass transition temperature of vinyl resin should be within the range of -40°C to 100°C, and the number average molecular weight should be 1.
Within the range of 000 to 8000, preferably 2000 to 60
It was also found that it should be within the range of 00.
このようなビニル樹脂を、基体樹脂と硬化剤とを主成分
とする熱硬化性樹脂組成物のうち基体樹脂の重量に対し
、約０．５〜１０重量％、好ましくは１〜５重量％含有
せしめることにより硬化塗膜の平滑性、光沢、鮮映性等
の外観が著しく改善せられる。ビニル樹脂の添加量が熱
硬化性塗体塗料用樹脂組成物重量に対し、０．５％未満
ではビニル樹脂添加の効果が充分ではなく、また１０重
量％をこえると、耐候性、耐衝撃性等塗膜物性の低下が
認められ望ましくない。Such a vinyl resin is contained in a thermosetting resin composition mainly composed of a base resin and a curing agent, based on the weight of the base resin, about 0.5 to 10% by weight, preferably 1 to 5% by weight. The appearance of the cured coating film, such as its smoothness, gloss, and sharpness, can be significantly improved by applying it. If the amount of vinyl resin added is less than 0.5% based on the weight of the resin composition for thermosetting paint, the effect of adding vinyl resin will not be sufficient, and if it exceeds 10% by weight, the weather resistance and impact resistance will deteriorate. This is undesirable as a decrease in the physical properties of the coating film is observed.
ビニル樹脂は粉体塗料を製造する工程のうち、粉体塗料
組成物を溶融分散する工程までの任意の段階で添加、配
合せしめればよい。The vinyl resin may be added and blended at any stage of the process of producing a powder coating up to the process of melting and dispersing the powder coating composition.
粉体塗料はクリヤーであっても着色であってもかまわず
、又通常粉体塗料に添加せられる任意の助剤を加えるこ
ともできる。例えば塗料で通常使用されている各種の無
機ならびに有機顔料が用いられ、無機顔料としては例え
ば亜鉛華、カーボンブラック、酸化チタン、アンチモン
白、鉄黒、ベンガラ、鉛丹、カドミウムエロー、硫化亜
鉛、リトポン、硫酸バリウム、硫酸鉛、炭酸バリウム、
鉛白、アルミナホワイト等が、又有機顔料としてはアゾ
系、ポリ縮合アゾ系、メタルコンプレックスアゾ系、ベ
ンズイミダシロン系、フタロシアニン系（ブルー、グリ
ーン）、チオインジゴ系、アンスラキノン系、フラバン
スロン系、インダンスレン系、アンスラピリジン系、ピ
ランスロン系、インインドリノン系、ペリレン系、ペリ
ノン系およびキナクリドン系の各種顔料が有利に用いら
れる。しかしながらこれらは単なる例示で通常使用され
る顔料はすべて適用可能で、特に限定されるものはない
。The powder coating may be clear or colored, and any auxiliary agents that are normally added to powder coatings may also be added. For example, various inorganic and organic pigments commonly used in paints are used, and inorganic pigments include zinc white, carbon black, titanium oxide, antimony white, iron black, red iron oxide, red lead, cadmium yellow, zinc sulfide, and lithopone. , barium sulfate, lead sulfate, barium carbonate,
Lead white, alumina white, etc., and organic pigments such as azo, polycondensed azo, metal complex azo, benzimidacylon, phthalocyanine (blue, green), thioindigo, anthraquinone, and flavanthrone. , indanthrene, anthrapyridine, pyranthrone, inindolinone, perylene, perinone and quinacridone pigments are advantageously used. However, these are merely examples, and all commonly used pigments are applicable, and there are no particular limitations.
また本発明の粉体塗料組成物には、エポキシ、ポリエス
テル、ポリアミド等の樹、脂、或は繊維素誘導体の如き
各種樹脂、顔料、流動調整剤、ブロッキング防止剤、紫
外線吸収剤、ベンゾイン、帯電防止剤、酸化防止剤等の
通常用いられる塗料用添加物を必要に応じて１種または
２種以上加えることができ、添加物を加え、または加え
ずして粉体塗料として実用に供せられる。The powder coating composition of the present invention also contains resins such as epoxy, polyester, and polyamide, resins, various resins such as cellulose derivatives, pigments, flow regulators, antiblocking agents, ultraviolet absorbers, benzoin, and electrostatic charges. One or more types of commonly used coating additives such as inhibitors and antioxidants can be added as necessary, and the powder coating can be put to practical use with or without additives. .
本発明の粉体塗料は、上述の基体樹脂、硬化剤、および
ビニル樹脂の必須三成分、及び必要に応じ各種樹脂、顔
料、流動調整剤、ブロッキング防止剤、紫外線吸収剤、
ベンゾイン、帯電防止剤、酸化防止剤等を適宜混合した
後、通常加熱ロール、エクストルーダーの如き、溶融混
線機で溶融混合し、冷却の後粉砕して粉体塗料とする。The powder coating of the present invention contains the above-mentioned three essential components of the base resin, curing agent, and vinyl resin, as well as various resins, pigments, fluidity regulators, antiblocking agents, ultraviolet absorbers,
After suitably mixing benzoin, an antistatic agent, an antioxidant, etc., the mixture is melt-mixed using a melt mixer, such as a heating roll or an extruder, and is cooled and pulverized to form a powder coating.
また、塗装については、静電吹付法、流動浸漬法等の周
知の塗装方法によって被塗物に塗装し、通常これを１５
０〜２１０℃の焼付炉で焼付を行い粉体塗装による塗膜
を得ることができる。Regarding painting, the object to be coated is coated using well-known coating methods such as electrostatic spraying and fluidized dipping.
A powder coating film can be obtained by baking in a baking oven at 0 to 210°C.
かくして得られる硬化塗膜はビニル樹脂を添加しない系
、あるいは従来の表面調整剤を加えた系に比し、塗膜平
滑性、光沢、鮮映性の著しい改善が認められ自動車塗装
等に極めて有用である。The cured coating film obtained in this way has significant improvements in coating smoothness, gloss, and sharpness compared to systems without vinyl resin or systems with conventional surface conditioners added, making it extremely useful for automotive coatings, etc. It is.
以下実施例により本発明を説明する。The present invention will be explained below with reference to Examples.
−１（アクリル 脂のム成）
表−１の参考例１の配合にしたがい、滴下ロート、攪拌
翼、温度計を備えたフラスコにキシレン９５重量部を仕
込、１３０℃に加熱した。滴下ロートを用いて、スチレ
ン２５部、メチルメタクリレート２７部、グリシジルメ
タクリレート３０部、２−エチルへキシルメチクリレー
ト１８部、開始剤カヤエステル０４部の溶液を上記フラ
スコに３時間で等速滴下した０滴下終了後３０分間保持
の後、キシレン４部、カヤエステルｏ ０９４部を滴下
ロートを用いて１時間で等速滴下した０滴下終了後、さ
らに１３０℃で２時間保持の後、キシレンを減圧蒸留
参考例−２の合成法に従い、表−１の配合でアクによ
り除去してアクリル樹脂Ａを得た。 リル
樹脂Ｃ，Ｄを得た。-1 (Acrylic fat composition) According to the formulation of Reference Example 1 in Table 1, 95 parts by weight of xylene was charged into a flask equipped with a dropping funnel, a stirring blade, and a thermometer, and heated to 130°C. Using a dropping funnel, a solution of 25 parts of styrene, 27 parts of methyl methacrylate, 30 parts of glycidyl methacrylate, 18 parts of 2-ethylhexyl methacrylate, and 04 parts of initiator Kayaester was dropped into the flask at a constant rate over 3 hours. After the completion of the zero drop, hold for 30 minutes, then drop 4 parts of xylene and 0.94 parts of Kaya Ester O at a uniform rate over 1 hour using a dropping funnel. distillation
According to the synthesis method of Reference Example 2, acrylic resin A was obtained by removing with a lye according to the formulation shown in Table 1. Riru resins C and D were obtained.
−２（アクリル のム成）
表−１の参考例２の配合にしたがい、滴下ロート、攪拌
翼、温度計を備えたフラスコにキシレン９５重量部を仕
込、１３０℃に加熱した。滴下ロートを用いて、メチル
メタクリレート３４部、スチレン２０部、グリシジルメ
タクリレート３０部、ｎ−ブチルメタクリレート１０部
、開始剤カヤエステル０４部の溶液を上記フラスコに３
時間で等速滴下した。滴下終了後３０分間保持の後、キ
シレン４部、カヤエステルＯ０１４部を滴下ロートを用
いて１時間で等速滴下した。滴下終了後、さらに１３０
℃で２時閏保持の後、これらの溶液を１３０℃に保持し
た時にプチルアシッドホスヘート３部、キシレン１０部
を１時間で滴下した後、減圧蒸留により除去してアクリ
ル樹脂Ｂを得た。-2 (Acrylic composition) According to the formulation of Reference Example 2 in Table 1, 95 parts by weight of xylene was charged into a flask equipped with a dropping funnel, a stirring blade, and a thermometer, and heated to 130°C. Using a dropping funnel, a solution of 34 parts of methyl methacrylate, 20 parts of styrene, 30 parts of glycidyl methacrylate, 10 parts of n-butyl methacrylate, and 04 parts of initiator Kayaester was added to the above flask.
It was dropped at a uniform rate over time. After the dropwise addition was completed and held for 30 minutes, 4 parts of xylene and 14 parts of Kayaester O0 were added dropwise at a constant rate over 1 hour using a dropping funnel. After the completion of dripping, another 130
After holding the solution at 130°C for 2 hours, 3 parts of butyl acid phosphate and 10 parts of xylene were added dropwise over 1 hour and removed by vacuum distillation to obtain acrylic resin B.
−３〜４（アクリル のム成）
前例−５〜８（アクリル 脂のム成）
参考例−１の合成法に従い、表−１の配合でアクリル樹
脂Ｅ、Ｆ、Ｇ、Ｈを得た。-3 to 4 (acrylic resin composition) Examples -5 to 8 (acrylic resin composition) Acrylic resins E, F, G, and H were obtained according to the synthesis method of Reference Example 1 and with the formulations shown in Table 1.
−１（アクリル 体塗料の調製）
アクリル樹脂Ａ１００重量部、デカンジカルボン酸２４
部、レベリング剤Ｅ ２部をヘンシェルミキサー（三井
三池製作所社製）にて乾式混合し、ついでコニーグーＰ
Ｒ−４６（スイス：ブス社製）にて１００℃の温度で溶
融分散し、冷却後ハンマーミルにて粉砕し１５０メツシ
ユの金網で分級してアクリル粉体塗料を得た。-1 (Preparation of acrylic paint) 100 parts by weight of acrylic resin A, 24 parts by weight of decanedicarboxylic acid
1 part and 2 parts of leveling agent E were dry mixed in a Henschel mixer (manufactured by Mitsui Miike Seisakusho Co., Ltd.), and then Coney Goo P
The mixture was melted and dispersed at a temperature of 100° C. using R-46 (manufactured by Buss AG, Switzerland), cooled, crushed using a hammer mill, and classified using a 150-mesh wire mesh to obtain an acrylic powder coating.
こうしてできた粉体塗料を鉄板に静電塗装し、１６０℃
で２０分間焼付けて膜厚的８０μの硬化塗板を得た。The powder paint made in this way was electrostatically coated on an iron plate and heated to 160°C.
A cured coated plate having a film thickness of 80 μm was obtained by baking for 20 minutes.
このようにしてできた塗板の外観（肌）と物性（耐衝撃
性）を評価した結果、良好な外観を確認した。またこの
結果は、表−２に記述した。As a result of evaluating the appearance (skin) and physical properties (impact resistance) of the coated plate made in this way, it was confirmed that it had a good appearance. The results are also described in Table-2.
−２（アクリル 塗 の ）
アクリル樹脂Ｂ１００重量部、デカンジカルボン酸２４
部、酸化チタンＣＲ５０（万態産業社製）３０部、レベ
リング剤Ｅ ２部をヘンシェルミキサー（三井三池製作
所社製）にて乾式混合し、ついでコニーグーＰＲ−４６
（スイス：ブス社製）にて１００℃の温度で溶融分散し
、冷却後ハンマーミルにて粉砕し１５０メツシユの金網
で分級してアクリル粉体塗料を得た。-2 (acrylic coating) Acrylic resin B 100 parts by weight, decanedicarboxylic acid 24
1 part, 30 parts of titanium oxide CR50 (manufactured by Bancho Sangyo Co., Ltd.), and 2 parts of leveling agent E were dry mixed in a Henschel mixer (manufactured by Mitsui Miike Seisakusho Co., Ltd.), and then Coney Goo PR-46
(manufactured by Buss, Switzerland) at a temperature of 100° C., cooled, crushed in a hammer mill, and classified with a 150-mesh wire mesh to obtain an acrylic powder coating.
こうしてできた粉体塗料を鉄板に静電塗装し、１６０℃
で２０分間焼付けて膜厚的８０μの硬化塗板を得た。The powder paint made in this way was electrostatically coated on an iron plate and heated to 160°C.
A cured coated plate having a film thickness of 80 μm was obtained by baking for 20 minutes.
このようにしてできた塗板の外観（肌）と物性（耐衝撃
性）を評価した結果、良好な外観を確認した。またこの
結果は、表−２に記述した。As a result of evaluating the appearance (skin) and physical properties (impact resistance) of the coated plate made in this way, it was confirmed that it had a good appearance. The results are also described in Table-2.
−３〜５ ア リル −粁瞭［
実施例２の調整法にならい表−２の配合でアクリル粉体
塗料を得る。-3 to 5 allyl - 粁平 [An acrylic powder coating was obtained according to the preparation method of Example 2 and the formulation shown in Table 2.
こうしてできな粉体塗料を鉄板に静電塗装し、１６０℃
で２０分間焼付けて膜厚的８０μの硬化塗板を得た。The resulting powder paint was electrostatically applied to an iron plate and heated to 160°C.
A cured coated plate having a film thickness of 80 μm was obtained by baking for 20 minutes.
このようにしてできた塗板の外観（肌）と物性（耐衝撃
性）を評価した結果、良好な外観を確認した。またこの
結果は・、表−２に記述した。As a result of evaluating the appearance (skin) and physical properties (impact resistance) of the coated plate made in this way, it was confirmed that it had a good appearance. The results are also described in Table 2.
例−６（ポリエステル塗 の調製）
滴下ロート、攪拌翼、温度計を備えたフラスコにＢ、Ｒ
６６１０（日本ポリエステル社製ポリエステル樹脂）１
００重量部、２官能エポキシＥ ＲＬ −４２３４（ユ
ニオンカーバイド社製）５部を仕込み加熱し１２０℃で
１時閏保持した後冷却しで取り出した。Example 6 (Preparation of polyester coating) In a flask equipped with a dropping funnel, a stirring blade, and a thermometer,
6610 (polyester resin manufactured by Nippon Polyester Co., Ltd.) 1
00 parts by weight and 5 parts of bifunctional epoxy E RL-4234 (manufactured by Union Carbide) were heated, held at 120° C. for 1 hour, cooled, and taken out.
こうしてできたポリエステル樹脂１０５重量部、フレラ
ンＵＩ （ＢＡＳＦ社製プ社製プロインクイソシアナー
ト部、酸化チタンＣＲ５０４０部をヘンシェルミキサー
（三°井三池製作所社製）にて乾式混合し、ついでコニ
ーグーＰＲ−４６（スイス：ブス社製）にて１００℃の
温度で溶融分散し、冷却後ハンマーミルにて粉砕し１５
０メツシユの金網で分級して粉体塗料を得た。105 parts by weight of the polyester resin thus produced, Fleran UI (pro-ink isocyanate part, manufactured by BASF Corporation, and 5040 parts of titanium oxide CR) were dry mixed in a Henschel mixer (manufactured by Miike Seisakusho Co., Ltd.), and then Coney Goo PR- 46 (manufactured by Buss, Switzerland) at a temperature of 100°C, and after cooling, the mixture was pulverized with a hammer mill.
A powder coating was obtained by classifying with a wire mesh of 0 mesh.
こうしてできた粉体塗料を鉄板に静電塗装し、１８０℃
で２０分間焼付けて膜厚的８０μの硬化塗板を得た。The powder paint made in this way was electrostatically coated on an iron plate and heated to 180°C.
A cured coated plate having a film thickness of 80 μm was obtained by baking for 20 minutes.
このようにしてできた塗板の外観（肌）と物性（耐衝撃
性）を評価した結果、良好な外観を確認した。またこの
結果は、表−２に記述した。As a result of evaluating the appearance (skin) and physical properties (impact resistance) of the coated plate made in this way, it was confirmed that it had a good appearance. The results are also described in Table-2.
−７（エポキシ塗料の ）
エポトートＹＤ−０１９（東部化成社製エポキシ樹脂）
１００重量部、ジシアンジアミド３部、酸化チタンＣＲ
５０４０部をヘンシェルミキサー（三井三池製作所社製
）にて乾式混合し、ついでコニーグーＰＲ−４６（スイ
ス：ブス社製）にて１００℃の温度で溶融分散し、冷却
後ハンマーミルにて粉砕し１５０メツシユの金網で分級
して粉体塗料を得た。-7 (Epoxy paint) Epotote YD-019 (Epoxy resin manufactured by Tobu Kasei Co., Ltd.)
100 parts by weight, 3 parts of dicyandiamide, CR titanium oxide
5,040 parts were dry mixed in a Henschel mixer (manufactured by Mitsui Miike Manufacturing Co., Ltd.), then melted and dispersed in a Coney Goo PR-46 (manufactured by Buss, Switzerland) at a temperature of 100°C, and after cooling, pulverized in a hammer mill to 150 parts. The powder paint was obtained by classifying it with mesh wire mesh.
こうしてできた粉体塗料を鉄板に静電塗装し、１８０℃
で２０分間焼付けて膜厚的８０μの硬化塗板を得た。The powder paint made in this way was electrostatically coated on an iron plate and heated to 180°C.
A cured coated plate having a film thickness of 80 μm was obtained by baking for 20 minutes.
このようにしてできた塗板の外観（肌）と物性、（耐衝
撃性）を評価した結果、良好な外観を確認した。またこ
の結果は、表−２に記述した。As a result of evaluating the appearance (skin), physical properties, and (impact resistance) of the coated plate thus produced, it was confirmed that it had a good appearance. The results are also described in Table-2.
−１（アクリル 塗 の ）
アクリル樹脂Ａ１００重量部、デカンジカルボン酸２４
部をヘンシェルミキサー（三井三池製作所社製）にて乾
式混合し、ついでコニーグーＰＲ−４６（スイス：ブス
社製）にて１００℃の温度で溶融分散し、冷却後ハンマ
ーミルにて粉砕し１５０メツシユの金網で分級してアク
リル粉体塗料を得た。-1 (acrylic coating) 100 parts by weight of acrylic resin A, 24 parts by weight of decanedicarboxylic acid
The parts were dry mixed using a Henschel mixer (manufactured by Mitsui Miike Manufacturing Co., Ltd.), then melted and dispersed in a Coney Goo PR-46 (manufactured by Buss, Switzerland) at a temperature of 100°C, and after cooling, pulverized with a hammer mill to give 150 mesh. The acrylic powder paint was obtained by classification using a wire mesh.
こうしてできな粉２体塗料を鉄板に静電塗装し、１６０
℃で２０分間焼付けて膜厚的８０μの硬化塗板を得た。The two powder paints thus obtained were electrostatically applied to the iron plate, and 160
A cured coated plate having a film thickness of 80 μm was obtained by baking at ℃ for 20 minutes.
このようにしてできた塗板の外観（肌）と物性（耐衝撃
性）を評価した結果、不良な外観を確認した。またこの
結果は、表−３に記述した。As a result of evaluating the appearance (skin) and physical properties (impact resistance) of the coated plate made in this way, it was confirmed that the appearance was poor. The results are also described in Table-3.
例−２（アクリル 塗 の
アクリル樹脂８１００重量部、デカンジカルボン酸２４
部、酸化チタンＣＲ５０（石層産業社製）３０部をヘン
シェルミキサー（三井三池製作所社製）にて乾式混合し
、ついでコニーグーＰＲ−４６（スイス：ブス社製）に
て１００℃の温度で溶融分散し、冷却後ハンマーミルに
て粉砕し１５０メツシユの金網で分級してアクリル粉体
塗料を得た。Example-2 (8100 parts by weight of acrylic resin, 24 parts by weight of decanedicarboxylic acid)
and 30 parts of titanium oxide CR50 (manufactured by Ishiya Sangyo Co., Ltd.) were dry mixed in a Henschel mixer (manufactured by Mitsui Miike Seisakusho Co., Ltd.), and then melted at a temperature of 100°C in a Coney Goo PR-46 (manufactured by Buss, Switzerland). After being dispersed and cooled, it was crushed in a hammer mill and classified using a 150-mesh wire mesh to obtain an acrylic powder coating.
こうしてできた粉体塗料を鉄板に静電塗装し、１６０℃
で２０分間焼付けて膜厚的８０μの硬化塗板を得た。The powder paint made in this way was electrostatically coated on an iron plate and heated to 160°C.
A cured coated plate having a film thickness of 80 μm was obtained by baking for 20 minutes.
このようにしてできた塗板の外観（肌）と物性（耐衝撃
性）を評価した結果、不良な外観を確認した。またこの
結果は、表−３に記述した。As a result of evaluating the appearance (skin) and physical properties (impact resistance) of the coated plate made in this way, it was confirmed that the appearance was poor. The results are also described in Table-3.
−３〜７（アクリル 塗 の
実施例２の調整法にならい表−３の配合でアクリル粉体
塗料を得る。-3 to 7 (Acrylic powder coatings were obtained using the formulations shown in Table 3 following the preparation method of Example 2 for acrylic coatings.
こうしてできた粉体塗料を鉄板に静電塗装し、１６０℃
で２０分間焼付けて膜厚的８０μの硬化塗板を得た。The powder paint made in this way was electrostatically coated on an iron plate and heated to 160°C.
A cured coated plate having a film thickness of 80 μm was obtained by baking for 20 minutes.
このようにしてできた塗板の外観（肌）と物性（耐衝撃
性）を評価した結果、不良な外観を確認した。またこの
結果は、表−３に記述した。As a result of evaluating the appearance (skin) and physical properties (impact resistance) of the coated plate made in this way, it was confirmed that the appearance was poor. The results are also described in Table-3.
較例−８（ポリエステル塗 の ）
滴下ロート、攪拌翼、温度計を備えたフラスコにＥ Ｒ
６６１０（日本ポリエステル社製ポリエステル樹脂）１
００重量部、２官能エポキシＥ ＲＬ −４２３４（ユ
ニオンカーバイド社製）５部を仕込み加熱し１２０℃で
１時間保持した後冷却して取り出した。Comparative Example 8 (polyester coated) A flask equipped with a dropping funnel, stirring blade, and thermometer was
6610 (polyester resin manufactured by Nippon Polyester Co., Ltd.) 1
00 parts by weight and 5 parts of bifunctional epoxy E RL-4234 (manufactured by Union Carbide) were heated, held at 120°C for 1 hour, cooled, and taken out.
こうしてできたポリエステル樹脂１０５重量部、フレラ
ンＵＩ （ＢＡＳＦ社製ブロックイソシアナート）３６
部、酸化チタンＣＲ５０４０部をヘンシェルミキサー（
三井三池製作所社製）にて乾式混合し、ついでコニーグ
ーＰＲ−４６（スイス：ブス社製）にて１００℃の温度
で溶融分散し、冷却後ハンマーミルにて粉砕し１５０メ
ツシユの金網で分級して粉体塗料を得た。105 parts by weight of the polyester resin thus produced, 36 parts by weight of Fleran UI (block isocyanate manufactured by BASF)
parts, titanium oxide CR5040 parts were mixed in a Henschel mixer (
The mixture was dry mixed in a Mitsui Miike Seisakusho Co., Ltd.), then melted and dispersed in a Coney Goo PR-46 (Buss, Switzerland) at a temperature of 100°C, cooled, pulverized in a hammer mill, and classified with a 150-mesh wire mesh. A powder coating was obtained.
こうしてできた粉体塗料を鉄板に静電塗装し、１８０℃
で２０分間焼付けて膜厚的８０μの硬化塗板を得た。The powder paint made in this way was electrostatically coated on an iron plate and heated to 180°C.
A cured coated plate having a film thickness of 80 μm was obtained by baking for 20 minutes.
このようにしてできた塗板の外観（肌）と物性（耐衝撃
性）を評価した結果、不良な外観を確認した。またこの
結果は、表−３に記述した。As a result of evaluating the appearance (skin) and physical properties (impact resistance) of the coated plate made in this way, it was confirmed that the appearance was poor. The results are also described in Table-3.
−９エポキシ塗 の
エボトートＹＤ−０１９（東部化成社製エポキシ樹脂）
１００重量部、ジシアンジアミド３部、酸化チタンＣＲ
５０４０部をヘンシェルミキサー（三井三池製作所社製
）にて乾式混合し、ついでコニーグーＰＲ−４６（スイ
ス：ブス社製）にて１００℃の温度で溶融分散し、冷却
後ハンマーミルにて粉砕し１５０メツシユの金網で分級
して粉体塗料を得た。-9 Epoxy coating Evotote YD-019 (epoxy resin manufactured by Tobu Kasei Co., Ltd.)
100 parts by weight, 3 parts of dicyandiamide, CR titanium oxide
5,040 parts were dry mixed in a Henschel mixer (manufactured by Mitsui Miike Manufacturing Co., Ltd.), then melted and dispersed in a Coney Goo PR-46 (manufactured by Buss, Switzerland) at a temperature of 100°C, and after cooling, pulverized in a hammer mill to 150 parts. The powder paint was obtained by classifying it with mesh wire mesh.
こうしてできた粉体塗料を鉄板に静電塗装し、１８０℃
で２０分間焼付けて膜厚的８０μの硬化塗板を得た。The powder paint made in this way was electrostatically coated on an iron plate and heated to 180°C.
A cured coated plate having a film thickness of 80 μm was obtained by baking for 20 minutes.
このようにしてできた塗板の外観（肌）と物性（耐衝撃
性）を評価した結果、不良な外観を確認した。またこの
結果は、表−３に記述した。As a result of evaluating the appearance (skin) and physical properties (impact resistance) of the coated plate made in this way, it was confirmed that the appearance was poor. The results are also described in Table-3.
［評価方法コ
１）肌（平滑性）
■目視：［判断基準］
良好 −一〇
やや不良−−Δ
不良 −−×
■Ｒａ（表面中心粗さ）
膜厚８０μｍにはおいて表面粗度計で測定して得られる
値で、下図の斜線面積Ｓを長さしで除した数値→平滑で
なくなるとこの数値が大きくなる
Ｓ：斜線部の面積合計
Ｒａ＝ＴＴ
２）物性（耐衝撃性）
５００ｇのおもりをのせた１７２インチの硬球を、水平
に維持した塗板の垂直上方から落下させた時どの程度の
高さに耐え得るかを測定したもの。[Evaluation method 1) Skin (smoothness) ■Visual observation: [Judgment criteria] Good - 10 Slightly poor - Δ Poor - - × ■Ra (Surface center roughness) At a film thickness of 80 μm, it was measured with a surface roughness meter. The value obtained by measurement is the value obtained by dividing the shaded area S in the figure below by the length → This value will increase if it is not smooth S: Total area of the shaded area Ra = TT 2) Physical properties (impact resistance) 500g A 172-inch hard ball with a weight on it was dropped from vertically above a horizontally held painted board, and the height it could withstand was measured.
Claims (1)
脂と、エポキシ用の硬化剤とからなる熱硬化性塗体塗料
用樹脂組成物に、チオリンゴ酸、マレイン酸、フマル酸
およびイタコン酸からなる群より選ばれる少なくとも１
種の脂肪族ジカルボン酸成分を重量比で１〜１０％含む
数平均分子量１０００〜８０００、ガラス転移温度−４
０〜１００℃のビニル樹脂を０．５〜１０重量％配合し
てなる樹脂組成物を樹脂成分として含む粉体塗料組成物
（２）基体樹脂が０．０５〜１０％の酸性リン酸エステ
ルで変性されたアクリル樹脂、ポリエステル樹脂または
エポキシ樹脂である請求項第１項記載の組成物 （３）基体樹脂がグリシジル基含有単量体２０〜５０重
量％と他のα，β−エチレン性不飽和単量体８０〜５０
重量％の共重合で得られる、ガラス転移温度３０〜７５
℃、数平均分子量１５００〜１００００のビニル樹脂で
ある請求項第１項または第２項記載の組成物[Scope of Claims] (1) A resin composition for a thermosetting paint consisting of a base resin having two or more oxirane groups in one molecule and a curing agent for epoxy, including thiomalic acid, maleic acid, At least one selected from the group consisting of fumaric acid and itaconic acid
Contains 1-10% by weight of aliphatic dicarboxylic acid component, number average molecular weight 1000-8000, glass transition temperature -4
Powder coating composition containing a resin composition containing 0.5 to 10% by weight of vinyl resin at 0 to 100°C as a resin component (2) The base resin is 0.05 to 10% of acidic phosphoric acid ester. The composition (3) according to claim 1, wherein the base resin is a modified acrylic resin, polyester resin or epoxy resin, and the base resin comprises 20 to 50% by weight of a glycidyl group-containing monomer and other α,β-ethylenically unsaturated substances. Monomer 80-50
Glass transition temperature obtained by copolymerization of 30 to 75% by weight
The composition according to claim 1 or 2, which is a vinyl resin having a number average molecular weight of 1,500 to 10,000.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2171897A JPH0459878A (en) | 1990-06-28 | 1990-06-28 | Powder coating composition |
| CA002045813A CA2045813A1 (en) | 1990-06-28 | 1991-06-27 | Powder coating composition |
| AU79379/91A AU647488B2 (en) | 1990-06-28 | 1991-06-27 | A powder coating composition |
| EP91305913A EP0465176B1 (en) | 1990-06-28 | 1991-06-28 | A powder coating composition |
| DE69119829T DE69119829T2 (en) | 1990-06-28 | 1991-06-28 | Powder coating composition |
| KR1019910010886A KR920000893A (en) | 1990-06-28 | 1991-06-28 | Powder coating composition |
| US08/514,891 US5576389A (en) | 1990-06-28 | 1995-08-14 | Powder coating composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2171897A JPH0459878A (en) | 1990-06-28 | 1990-06-28 | Powder coating composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0459878A true JPH0459878A (en) | 1992-02-26 |
Family
ID=15931840
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2171897A Pending JPH0459878A (en) | 1990-06-28 | 1990-06-28 | Powder coating composition |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5576389A (en) |
| EP (1) | EP0465176B1 (en) |
| JP (1) | JPH0459878A (en) |
| KR (1) | KR920000893A (en) |
| AU (1) | AU647488B2 (en) |
| CA (1) | CA2045813A1 (en) |
| DE (1) | DE69119829T2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6494429B2 (en) | 1997-08-04 | 2002-12-17 | Canon Kabushiki Kaisha | Panel support structure, display panel supported by panel support structure, and image forming apparatus using display panel |
| KR100609094B1 (en) * | 1997-12-31 | 2006-12-04 | 주식회사 케이씨씨 | Powder Coating Composition |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU651007B2 (en) * | 1991-10-29 | 1994-07-07 | Courtaulds (Australia) Pty Ltd | Solventless coating |
| US6093774A (en) * | 1997-09-26 | 2000-07-25 | Reichhold Chemicals, Inc. | Low gloss powder coating composition |
| US6201052B1 (en) * | 1998-11-25 | 2001-03-13 | The Lubrizol Corporation | Powder-coating compositions containing transfer efficiency-enhancing additives |
| US6388012B1 (en) | 1999-04-13 | 2002-05-14 | Mitsui Chemicals, Inc. | Thermosetting powder resin composition |
| US6541544B1 (en) * | 2000-05-26 | 2003-04-01 | H. B. Fuller Licensing & Financing, Inc. | Textured weatherable powder coatings |
| US7034075B1 (en) * | 2000-11-28 | 2006-04-25 | H. B. Fuller Licensing & Financing Inc. | Low gloss powder coating compositions |
| ES2266417T3 (en) | 2001-10-11 | 2007-03-01 | Rohm And Haas Company | COMPOSITION OF POWDER COATING, PROCEDURE TO CURE THE SAME AND ARTICLES DERIVED FROM THE SAME. |
| JP4487689B2 (en) | 2004-08-26 | 2010-06-23 | 日産自動車株式会社 | Alumina particles, method for producing alumina particles, resin composition, and method for producing resin composition |
| JP4940556B2 (en) * | 2004-09-07 | 2012-05-30 | 日産自動車株式会社 | Resin composition |
| JP2007031684A (en) * | 2005-06-22 | 2007-02-08 | Nissan Motor Co Ltd | Resin composition and method of producing resin composition |
| EP2076566B1 (en) * | 2006-10-13 | 2011-08-31 | 3M Innovative Properties Company | Powder coating fluoropolymer compositions containing mono-hydroxy aromatic materials |
| WO2009142900A1 (en) * | 2008-05-22 | 2009-11-26 | Dow Global Technologies Inc. | Epoxy resin reactive diluent compositions |
| CN103087603B (en) * | 2013-01-23 | 2015-04-15 | 浙江德尚化工科技有限公司 | Amino stoving varnish capable of being cured quickly at low temperature |
| CN103087604B (en) * | 2013-01-23 | 2015-04-15 | 浙江德尚化工科技有限公司 | Functional additive for amino baking varnishes and preparation method thereof |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4321335A (en) * | 1979-06-19 | 1982-03-23 | Dainippon Ink & Chemicals, Inc. | Powder coating resin composition |
| US4661559A (en) * | 1983-05-20 | 1987-04-28 | Union Carbide Corporation | Impact resistant matrix resins for advanced composites |
| US5008335A (en) * | 1985-08-07 | 1991-04-16 | Ppg Industries, Inc. | Powder coating compositions of polyepoxides, acrylic copolymers and aliphatic or polyester dibasic acids |
| US4937288A (en) * | 1986-09-29 | 1990-06-26 | Ppg Industries, Inc. | Powder coating composition |
| US5055524A (en) * | 1987-07-16 | 1991-10-08 | Ppg Industries, Inc. | Polyol-modified polyanhydride curing agent for polyepoxide powder coatings |
| EP0340019B1 (en) * | 1988-04-28 | 1995-11-15 | Dainippon Ink And Chemicals, Inc. | Resin composition |
| US5034432A (en) * | 1988-12-29 | 1991-07-23 | Nippon Paint Co., Ltd. | Powder coatings |
| US5098955A (en) * | 1989-09-18 | 1992-03-24 | Ppg Industries, Inc. | Powder coating composition low Tg and high Tg polymers with acid groups |
-
1990
- 1990-06-28 JP JP2171897A patent/JPH0459878A/en active Pending
-
1991
- 1991-06-27 AU AU79379/91A patent/AU647488B2/en not_active Ceased
- 1991-06-27 CA CA002045813A patent/CA2045813A1/en not_active Abandoned
- 1991-06-28 KR KR1019910010886A patent/KR920000893A/en not_active Application Discontinuation
- 1991-06-28 EP EP91305913A patent/EP0465176B1/en not_active Expired - Lifetime
- 1991-06-28 DE DE69119829T patent/DE69119829T2/en not_active Expired - Fee Related
-
1995
- 1995-08-14 US US08/514,891 patent/US5576389A/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6494429B2 (en) | 1997-08-04 | 2002-12-17 | Canon Kabushiki Kaisha | Panel support structure, display panel supported by panel support structure, and image forming apparatus using display panel |
| KR100609094B1 (en) * | 1997-12-31 | 2006-12-04 | 주식회사 케이씨씨 | Powder Coating Composition |
Also Published As
| Publication number | Publication date |
|---|---|
| KR920000893A (en) | 1992-01-29 |
| CA2045813A1 (en) | 1991-12-29 |
| EP0465176B1 (en) | 1996-05-29 |
| EP0465176A1 (en) | 1992-01-08 |
| DE69119829T2 (en) | 1996-11-28 |
| AU7937991A (en) | 1992-01-02 |
| US5576389A (en) | 1996-11-19 |
| DE69119829D1 (en) | 1996-07-04 |
| AU647488B2 (en) | 1994-03-24 |
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